Methyl quinoline-5-carboxylate → Methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate

HRID 2173369ノート

反応式

HRID 2173369 の反応式
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1>C(O)(C(F)(F)F)=O.[Pt]=O>[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 1

HCID 12503486Methyl quinoline-5-carboxylate

生成物 1

HCID 77230270Methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 6422Trifluoroacetic acid溶媒

実験手順

Methyl quinoline-5-carboxylate (3.67 g, 19.61 mmol) was dissolved in TFA (60 ml) and added platinum oxide (0.49 g, 2.16 mmol) then hydrogenated at room temperature overnight. Filtered off the catalyst and evaporated to dryness. The residue was chromatographed through a 120 g ISCO Redi-sep column and eluted with 5% of (10% NH4OH in MeOH) in DCM to yield methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate 1H-NMR (600 MHz, CDCl3): δ ppm 8.42 (d, J=3.7 Hz, 1H), 7.485 (d, J=7.7 Hz, 1H), 7.06-7.08 (m, 1H), 3.82 (t, J=5.6 Hz, 1H), 3.72 (d, J=3.2 Hz, 3H), 3.02-2.93 (m, 1H), 2.88-2.93 (m, 1H), 2.16-2.20 (m, 1H), 1.97-2.05 (m, 2H), 1.85-1.90 (m, 1H); LC-MS: M+1=192.

後処理

  1. filtrationFiltered off the catalyst
  2. customevaporated to dryness
  3. customThe residue was chromatographed through a 120 g ISCO Redi-sep column
  4. washeluted with 5% of (10% NH4OH in MeOH) in DCM

出典と根拠

ORDレコード
ord-a4fe317fdaa545aaa5520b558deab614
出典データセット
uspto-grants-2015_06
特許番号
US09056859B2

反応ノート

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